Water insoluble azodyestuffs and process of making same



Patented May 17, 1932 UNITED STATES PATENT oFF-icE LEOPOLD LAsKA, ANnARTHuazIrs'cHEE, 0E QFEENBACH-ON-T'HE-MAIN, GERMANY,

ASSIGNORS r0 GENERAL ANILINE WORKS, I c., OF NEW YORK, N. Y., A CORPORA- TION OF DELAWARE 1 WATEB INSOLUBLE AZODYESTUFFS AND PROCESS OF MAKING SAME No Drawing. Application filed July 17, 1929, Serial No. 379,0(i0, and in Germany July 25, 1928.

Our invention relates to new azodyestufisv corresponding probably to the general formula:

mula v 7 OH -o 0-NHQQ-ualkyli wherein one X means hydrogen and the other X a methylgroup. The new dyestufl's'may be used for the production of valuable color lakes; when produced on the fiber they yield fast dyeings and printings. Compared with the known azodyestufi's derived from 2.3- hydroxynaphthoyl--amino-l-alkoxybenzene not containing a methyl group in 2 or 3 position the present new dyestuffs are distinguished surprisingly by such ani-Iicrease of the fastness to light, that already dyestufis obtained by combination with simple and cheap diazocompounds, such as meta-xylidine, show a remarkable iastness to light. Some of the dysteuifs in this series furthermore show a bright shade and a good fastness to kier boilmg. i a In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in centi;

15,2 parts of 4c-nitro-2-toluidine are diaz'o tized in the usual manner and the diazocompound is combined with a solution of 32,2

parts 7 of 2.3-hydroXynaphthoyl-4-amino-3- methyl-l-methoxybenzene in a dilute caustic sodasolution containing Turkey red oil and containing an amount of sodium acetate sufficient for binding the excess of the mineral 7 acid. The separated dyestuff corresponding probably tothe formula: g

INC:

on, v is filtered off and Washed. Mixed with the usual substrata it yields red color lakes of'a very good fastness to light.

Example 2 Cotton material previously treated in the usual manner is impregnated with a solution containing 9 grs. of 2.8-.hydroxynaphthoyl-4- amino-S-rnethyl-l-methoxybenzene, 18 cos. of a-caustic soda solution of 34 B6. and 15 cos. ofTurkey red oil in the lit er, and developed after having been squeezed oil, with a diazosolution containing 1,42 grs. of 5-chloro-2-toluidinein the liter and neutralized with sodiumacetate. The material isthen worked up as usually.

The dyestufi thus produced on the fiber corresponds probably to the formula:

I g V on; g Y It yields a bright bluish red dyeing of a very good fastness to light.

v and alkalies,

" 4-nitro-2-anisitline f Diazocompound of The following table gives the shades of some other dyestuffs derived from 2.3- hydroxynaphthoyl 4 amino 3 methyll-meththoxybenzene Diazocompound of Shade obtained m-x lidine Bluisli red m-c loroaniline Orange 2L5-dichloroaniline Brownish orange 2.4-dichloroaniline Full red 6-chloro-2-toluidine Yellowish red 4.6-clichloro-3-amino-toluene Dark red 2-nitroaniline Claret 3-nitroaniline' V r V Yellowish red 4-chl0ro-2-nitroaniline Full bluish claret 4.5-dich1oro-2-nitroaniline idem 3-nitro-4-toluidine r idem I 5-nitro-2-toluidine Claret Bluish red Dark bluish claret Garnet 5-nitr0-2-anisidin-e l-aminoanthraquinone Brownish red o-amin'oazotoluene Bluisli garnet 4-aminm4-nitro-2.5-dlmethoxy- Black azobenzene dianisidine (subsequently treated Dark blue with copper) V f Derived from 213-hydroXynaphth0yl-4- amino3-methyll ethoxybenzene Shade obtained Yellowlsh brown m-chloroan'iline Browmsh orange L's-dichloroaniline 4-chloro- 2-toluidine Scarlet 2.5-dichlor0-4-toluidine Brown 4.6-rlicl1lor-3-toluicline Bluish red l-chloro-2-amin0diphenylether Scarlet 2.4.5-trichloroaniline Brown 2-nit1'0aniline Orange-brown 4-chloro-5-bromo-2-t0luldine Full red Full bluish red 5-nitro-2-toluicline Browmsh red l-aminoanthraquinone Derived from 2.3-hydroxy'naphthoyl-4- amino-3-methyl-phenyl-n-butylether Diazocompound 0t Shade obtained 5 chloro-2 toluidine Red 2.5-dichlor'oanlline Brownish orange 2.4.5-trichloroaniline Full red 2-nitroan1l1ne Brownish" red 5-nitro-2-anisii1ine l-aminoanthraquinone Bluish claret r Brownish red Since an object of the present invention is to provide dyestuffs of good fastness properties, which dyestuffs are insoluble in water it is to be understood that the aromatic nuclei of the general formulae appearing in the appended claims contain no substituents as are known to render organic compounds soluble in water or alkalies and to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are the sulfonic acid, the carboxylic acid and the hydroxy group.

We claim:

1. A process which comprises combining a diazotized aromatic amino compound with a 2.3ehydroxynaphthoyll-aminod-alkoxymethylbenzene of the general formula:

wherein one X means hydrogen and the other X a methylgroup. a

2. As new compounds azodyestufis corresponding probably to the general formula.

wherein one X means hydrogen and the other X a methylgroup and aryl represents the residue of an aromatic diazotizable aminocompound, which dyestuffs yield when mixed with the usual substrata valuable orange to red to blue to black color lakes and orange to red-to blue to black dyeings fast to light when produced on the fiber.

3. As new compounds azodyestufis correw sponding probably to the general formula:

- N =Naryl lOC wherein-ary-lrepresents the residue of an aromatic diazotizable aminocompound, which dyestuffs yield when mixed with the usual substrata valuable orange to red to blue to black color lakesandorange to red to blue to black dyeings fast to light when produced on the fiber.

5. As new compounds azodyestuffs corre sponding probably to the general formula:

-'0 O-NHOOOH: C Ha i wherein X means an alkyl, alkoxy, aryloxy or nitro group or a halogen atom and this benzene nucleus may contain a further substituentof the group consisting of alkyl, alkoxy,

aryloxy, nitro or halogen, which dyestuffs yield whenmixed with the usual substrata 1910 valuable orange to red to blue to black color lakes and orange to red to blue to black dyegggs fast to light when produced on the er. 6. As new compounds azodyestufls corresponding probably to the general formula:

OH 0 o-NHp-o on,

wherein the benzene nucleus attached to the azogroup may contain a further substituent of the group consisting of alkyl, alkoxy, aryloxy, nitro or halogen, which dyestuffs yield when mixed with the usual substrata Valuable orange to red to blue to black color lakes and orange to red to blue to black dyeings fast to light when produced on the fiber.

7. As new compounds azodyestufls corresponding probably to the general formula:

wherein the benzene nucleus attached to the azogroup contains a further methylgroup or chlorine, which dyestufi's yield bright bluish red dyeings of a good fastness to light.

8. As a new compound the azodyestufl's corresponding probably to the formula:

on, N=NO01 OH 0 camp-0 OH: H:

which dyestufl' yields bright bluish red dyeings of a good fastness to light.

In testimony whereof, we alfix our signatures.

LEOPOLD LASKA. ARTHUR ZITSOHER. 

